Silanylamine-based compound, method of preparing the same and organic light emitting device including organic layer comprising the silanylamine-based compound

ABSTRACT

Silanylamine-based compounds represented by Formula 1 are provided. Methods of preparing the compounds and organic light emitting devices including organic layers comprising the silanylamine-based compounds are also provided. 
                         
The silanylamine-based compounds have excellent electrical stability and electron transporting capabilities. Thus, the silanylamine-based compounds may be effectively used for red, green, blue, and white fluorescent and phosphorescent materials used to form hole injection layers, hole transport layers, and emissive layers in organic light emitting devices. Organic light emitting devices using these compounds have high efficiency, low driving voltages, high luminance and long lifetimes.

CROSS-REFERENCE TO RELATED PATENT APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2006-0110187, filed on Nov. 8, 2006 in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to silanylamine-based compounds, methodsof preparing the same, and organic light emitting devices includingorganic layers comprising a silanylamine-based compound.

2. Description of the Related Art

Organic light emitting devices (OLEDs) are self-emitting devices havingwide viewing angles, excellent contrast, and quick responses. Organiclight emitting devices have low operating voltages and quick responsetimes, and can realize multi-color images. Accordingly, OLEDs are beingextensively researched.

A typical organic light emitting device has an anode/emissivelayer/cathode structure. Organic light emitting devices can also havevarious other structures, such as anode/hole transport layer/emissivelayer/cathode, and anode/hole transport layer/emissive layer/electroninjection layer/cathode. These alternative structures are realized byfurther including an electron transport layer and at least one of a holeinjection layer, a hole transport layer and an electron injection layerbetween the anode and the emissive layer, or between the emissive layerand the cathode.

Fluorene and anthracene derivatives have been used as to form the holetransport layer. However, organic light emitting devices having thesehole transport layers do not have satisfactory lifetime, efficiency, andpower consumption.

SUMMARY OF THE INVENTION

In one embodiment of the present invention, a material is provided forforming a red, green, blue, or white fluorescent or phosphorescentorganic layer of an organic light emitting device (OLED).

According to another embodiment, an OLED includes an organic layer usingthe material. The OLED using the material has excellent electricalstability, high electron transporting capability, high glass transitiontemperature, and crystallization prevention properties. The OLED alsoexhibits excellent efficiency, low operating voltage, high luminance andlong lifetime.

In yet another embodiment of the present invention, a method ofpreparing the material is provided.

According to one embodiment of the present invention, asilanylamine-based compound represented by Formula 1 below is provided.

In Formula 1, n is an integer ranging from 1 to 5 and X is selected froma single bond, substituted and unsubstituted C₁-C₃₀ alkylene groups,substituted and unsubstituted C₆-C₃₀ arylene groups, and substituted andunsubstituted C₂-C₃₀ heteroarylene groups. Ar₁ and Ar₂ are eachindependently selected from hydrogen atoms, substituted andunsubstituted C₆-C₃₀ aryl groups, and substituted and unsubstitutedC₂-C₃₀ heteroaryl groups. R₁, R₂ and R₃ are each independently selectedfrom hydrogen atoms, substituted and unsubstituted C₁-C₃₀ alkyl groups,substituted and unsubstituted C₂-C₃₀ alkenyl groups, substituted andunsubstituted C₂-C₃₀ alkynyl groups, substituted and unsubstitutedC₁-C₃₀ alkoxy groups, substituted and unsubstituted C₆-C₃₀ aryloxygroups, substituted and unsubstituted C₆-C₃₀ aryl groups, andsubstituted and unsubstituted C₂-C₃₀ heteroaryl groups. At least two ofR₁, R₂ and R₃ are bonded to each other to form a saturated orunsaturated ring.

According to another embodiment of the present invention, a method ofpreparing a silanylamine-based compound represented by Formula 1 isprovided. In one embodiment, the method includes reacting a compoundrepresented by Formula 1a and a compound represented by Formula 1b viaReaction Scheme 1 below.

In Formulae 1a and 1b, X, n, Ar₁, Ar₂, R₁, R₂ and R₃ are as describedabove, and Y is a halogen atom.

According to another embodiment of the present invention, an organiclight emitting device includes a first electrode, a second electrode,and an organic layer positioned between the first electrode and thesecond electrode, the organic layer including a silanylamine-basedcompound. The organic light emitting device including thesilanylamine-based compound represented by Formula 1 exhibits lowdriving voltage, excellent luminance, high efficiency, high currentdensity and has a long lifetime.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other features and advantages of the present inventionwill become more apparent by reference to the following detaileddescription when considered in conjunction with the attached drawings inwhich:

FIG. 1 is a schematic illustrating an organic light emitting deviceaccording to one embodiment of the present invention;

FIG. 2 is a graph of luminance according to driving voltage of organiclight emitting devices prepared according to Example 1 and ComparativeExample 1;

FIG. 3 is a graph of luminance according to driving voltage of organiclight emitting devices prepared according to Example 2 and ComparativeExample 1; and

FIG. 4 is a graph of luminance according to time of organic lightemitting devices prepared according to Example 3 and Comparative Example1.

DETAILED DESCRIPTION OF THE INVENTION

According to one embodiment of the present invention, asilanylamine-based compound is represented by Formula 1 below.

In Formula 1, an amine derivative is bonded to a silane derivativethrough a linking group —(X)_(n)— to form the silanylamine-basedcompound.

In Formula 1, n may be an integer ranging from 1 to 5 and X may beselected from a single bond, substituted and unsubstituted C₁-C₃₀alkylene groups, substituted and unsubstituted C₆-C₃₀ arylene groups,and substituted and unsubstituted C₂-C₃₀ heteroarylene groups. Ar₁ andAr₂ may be each independently selected from hydrogen atoms, substitutedand unsubstituted C₆-C₃₀ aryl groups, and substituted and unsubstitutedC₂-C₃₀ heteroaryl groups. R₁, R₂ and R₃ may be each independentlyselected from hydrogen atoms, substituted and unsubstituted C₁-C₃₀ alkylgroups, substituted and unsubstituted C₂-C₃₀ alkenyl groups, substitutedand unsubstituted C₂-C₃₀ alkynyl groups, substituted and unsubstitutedC₁-C₃₀ alkoxy groups, substituted and unsubstituted C₆-C₃₀ aryloxygroups, substituted and unsubstituted C₆-C₃₀ aryl groups, andsubstituted and unsubstituted C₂-C₃₀ heteroaryl groups. At least two ofR₁, R₂ and R₃ are optionally bonded to each other to form a saturated orunsaturated ring.

Nonlimiting examples of suitable unsubstituted C₁-C₃₀ alkyl groupsinclude methyl groups, ethyl groups, propyl groups, isobutyl groups,sec-butyl groups, pentyl groups, iso-amyl groups, and hexyl groups. Atleast one of the hydrogen atoms in the alkyl group may be substitutedwith a constituent selected from halogen atoms, hydroxy groups, nitrogroups, cyano groups, amino groups, amidino groups, hydrazines,hydrazones, carboxyl groups and salts thereof, sulfonic acid groups andsalts thereof, phosphoric acid groups and salts thereof, C₁-C₃₀ alkylgroups, C₁-C₃₀ alkenyl groups, C₁-C₃₀ alkynyl groups, C₆-C₃₀ arylgroups, C₇-C₂₀ arylalkyl groups, C₂-C₂₀ heteroaryl groups, C₃-C₃₀heteroarylalkyl groups, C₆-C₃₀ aryloxy groups and —N(Z₁)(Z₂). In the—N(Z₁)(Z₂) substituent, Z₁ and Z₂ may be each independently selectedfrom hydrogen atoms, substituted and unsubstituted C₁-C₃₀ alkyl groups,substituted and unsubstituted C₁-C₃₀ haloalkyl groups, substituted andunsubstituted C₆-C₃₀ aryl groups, substituted and unsubstituted C₆-C₃₀haloaryl groups, and substituted and unsubstituted C₂-C₃₀ heteroarylgroups.

The unsubstituted C₁-C₃₀ alkylene group is a bivalent linking grouphaving a structure similar to an alkyl group, and nonlimiting examplesof the alkylene group include methylene groups and ethylene groups. Atleast one hydrogen atom in the alkylene group may be substituted withany of the substituents described above in connection with theunsubstituted C₁-C₃₀ alkyl group.

Nonlimiting examples of the unsubstituted C₁-C₃₀ alkoxy group includemethoxy groups, ethoxy groups, phenyloxy groups, cyclohexyloxy groups,naphthyloxy groups, isopropyloxy groups, and diphenyloxy groups. Atleast one of the hydrogen atoms in the alkoxy group may be substitutedwith any of the substituents described above in connection with theunsubstituted C₁-C₃₀ alkyl group.

The C₂-C₃₀ alkenyl group is a hydrocarbon chain having a carbon-carbondouble bond in the center or at one end of the alkyl group structure.Nonlimiting examples of suitable alkenyl groups include ethylene groups,propylene groups, butylene groups, and hexylene groups. At least onehydrogen atom in the alkenyl group may be substituted with anysubstituent described above in connection with the unsubstituted C₁-C₃₀alkyl group.

The C₂-C₃₀ alkynyl group is a hydrocarbon chain having a carbon-carbontriple bond in the center or at one end of the alkyl group structure.Nonlimiting examples of suitable alkynyl groups include acetylenegroups, propylacetylene groups, phenylacetylene groups,naphthylacetylene groups, isopropylacetylene groups, t-butylacetylenegroups, and diphenylacetylene groups. At least one of the hydrogen atomsin the alkynyl group may be substituted with any substituent describedabove in connection with the unsubstituted C₁-C₃₀ alkyl group.

The C₆-C₃₀ aryl group is a carbocyclic aromatic system having from 6 to30 carbon atoms and including at least one aromatic ring. The rings canbe fused to each other or bonded to each other, for example, through asingle bond. At least one hydrogen atom in the aryl group may besubstituted with any of the substituents described above in connectionwith the unsubstituted C₁-C₃₀ alkyl group.

Nonlimiting examples of suitable unsubstituted C₆-C₃₀ aryl groupsinclude phenyl groups, C₁-C₁₀ alkylphenyl groups (e.g., ethylphenylgroups), halophenyl groups (e.g., o-, m- and p-fluorophenyl groups, anddichlorophenyl groups), cyanophenyl groups, dicyanophenyl groups,trifluoromethoxyphenyl groups, biphenyl groups, halobiphenyl groups,cyanobiphenyl groups, C₁-C₁₀ biphenyl groups, C₁-C₁₀ alkoxybiphenylgroups, o-, m- and p-tolyl groups, o-, m- and p-cumenyl groups, mesitylgroups, phenoxyphenyl groups, (α,α-dimethylbenzen)phenyl groups,(N,N′-dimethyl)aminophenyl groups, (N,N′-diphenyl)aminophenyl groups,pentalenyl groups, indenyl groups, naphthyl groups, halonaphthyl groups(e.g., fluoronaphthyl groups), C₁-C₁₀ alkylnaphthyl groups (e.g.,methylnaphthyl groups), C₁-C₁₀ alkoxynaphthyl groups (e.g.,methoxynaphthyl groups), cyanonaphthyl groups, anthracenyl groups,azulenyl groups, heptalenyl groups, acenaphthylenyl groups, phenalenylgroups, fluorenyl groups, anthraquinolyl groups, methylanthryl groups,phenanthrenyl groups, triphenylenyl groups, pyrenyl groups, chrysenylgroups, ethyl-chrysenyl groups, picenyl groups, perylenyl groups,chloroperylenyl groups, pentaphenyl groups, pentacenyl groups,tetraphenylenyl groups, hexaphenyl groups, hexacenyl groups, rubicenylgroups, coronenyl groups, trinaphthylenyl groups, heptaphenyl groups,heptacenyl groups, pyranthrenyl groups, and ovalenyl groups. At leastone of the hydrogen atoms in the aryl group may be substituted with anyof the substituents described above in connection with the unsubstitutedC₁-C₃₀ alkyl group.

The unsubstituted C₆-C₃₀ arylene group is a bivalent linking grouphaving a structure similar to the aryl group, and nonlimiting examplesof the arylene group include phenylene groups and naphthylene groups. Atleast one hydrogen atom in the arylene group may be substituted with anyof the substituents described above in connection with the unsubstitutedC₁-C₃₀ alkyl group.

The unsubstituted C₃-C₃₀ heteroaryl group is a group having at least onearomatic ring in which at least one carbon atom in the aryl group issubstituted with one of N, O, P and S. The aromatic rings can be fusedto each other or bonded to each other, for example, through a singlebond. At least one hydrogen atom in the heteroaryl group may besubstituted with any of the substituents described above in connectionwith the unsubstituted C₁-C₃₀ alkyl group.

Nonlimiting examples of the unsubstituted C₃-C₃₀ heteroaryl groupinclude pyrazolyl groups, imidazolyl groups, oxazolyl groups, thiazolylgroups, triazolyl groups, tetrazolyl groups, oxadiazolyl groups,pyridinyl groups, pyridazinyl groups, pyrimidinyl groups, triazinylgroups, carbazolyl groups, indolyl groups, quinolinyl groups, andisoquinolinyl groups. At least one hydrogen atom in the heteroaryl groupmay be substituted with any of the substituents described above inconnection with the unsubstituted C₁-C₃₀ alkyl group.

The unsubstituted C₃-C₆₀ heteroarylene group is a bivalent linking grouphaving a structure similar to the heteroaryl group, and at least onehydrogen atom in the heteroarylene group may be substituted with any ofthe substituents described above in connection with the unsubstitutedC₁-C₃₀ alkyl group.

The unsubstituted C₆-C₃₀ aryloxy group is a group represented by —OA,where A is the aryl group, such as a phenoxy group. At least onehydrogen atom in the aryloxy group may be substituted with any of thesubstituents described above in connection with the unsubstituted C₁-C₃₀alkyl group.

According to one embodiment of the present invention, in Formula 1, Xmay be selected from substituted and unsubstituted C₁-C₁₀ alkylenegroups, substituted and unsubstituted phenylene groups, substituted andunsubstituted naphthylene groups, substituted and unsubstitutedfluorenylene groups, substituted and unsubstituted anthracenylenegroups, substituted and unsubstituted pyridinylene groups, substitutedand unsubstituted quinolylene groups, substituted and unsubstitutedisoquinolylene groups, substituted and unsubstituted anthraquinolylenegroups, and substituted and unsubstituted carbazolylene groups.

Nonlimiting examples of suitable substituents for X include structuresshown in Formula 2 below.

In the structures shown in Formula 2, R₄ and R₅ are each independentlyselected from hydrogen atoms, halogen atoms, cyano groups, hydroxylgroups, substituted and unsubstituted C₁-C₃₀ alkyl groups, substitutedand unsubstituted C₁-C₃₀ alkoxy groups, substituted and unsubstitutedC₆-C₃₀ aryl groups, and substituted and unsubstituted C₃-C₃₀ heteroarylgroups. In one embodiment, for example, R₄ and R₅ are each independentlyselected from phenyl groups and halophenyl groups.

With X and n being as described above, nonlimiting examples of suitable—(X)_(n)— linking groups include the substituents shown in Formula 3below.

In the structures shown in Formula 3, Ar₁ and Ar₂ are each independentlyselected from substituted and unsubstituted C₁-C₁₂ aryl groups, andsubstituted and unsubstituted C₃-C₁₅ heteroaryl groups.

Nonlimiting examples of suitable substituents for Ar₁ and Ar₂ includephenyl groups, halophenyl groups, cyanophenyl groups, C₁-C₅ alkylphenylgroups, C₁-C₅ alkoxyphenyl groups, phenoxyphenyl groups, phenyl groupssubstituted with —N(Z₁)(Z₂), biphenyl groups, halobiphenyl groups,cyanobiphenyl groups, C₁-C₅ alkylbiphenyl groups, C₁-C₅ alkoxybiphenylgroups, biphenyl groups substituted with —N(Z₁)(Z₂), naphthyl groups,halonaphthyl groups, cyanonaphthyl groups, C₁-C₅ alkylnaphthyl groups,C₁-C₅ alkoxynaphthyl groups, phenoxynaphthyl groups, naphthyl groupssubstituted with —N(Z₁)(Z₂), fluorenyl groups, halofluorenyl groups,cyanofluorenyl groups, C₁-C₅ alkylfluorenyl groups, C₁-C₅alkoxyfluorenyl groups, phenoxyfluorenyl groups, carbazolyl groups,halocarbazolyl groups, cyanocarbazolyl groups, C₁-C₅ alkylcarbazolylgroups, C₁-C₅ alkoxycarbazolyl groups, phenoxycarbazolyl groups,carbazolyl groups substituted with —N(Z₁)(Z₂), C₆-C₁₂ arylcarbazolylgroups, C₆-C₁₂ haloarylcarbazolyl groups, pyridyl groups, halopyridylgroups, cyanopyridyl groups, C₁-C₅ alkylpyridyl groups, C₁-C₅alkoxypyridyl groups, phenoxypyridyl groups, and pyridyl groupssubstituted with —N(Z₁)(Z₂).

In the structures shown in Formula 3, nonlimiting examples of suitablesubstituents for Z₁ and Z₂ include hydrogen, substituted andunsubstituted C₁-C₃₀ alkyl groups, substituted and unsubstituted C₁-C₃₀haloalkyl groups, substituted and unsubstituted C₆-C₃₀ aryl groups,substituted and unsubstituted C₆-C₃₀ haloaryl groups, and substitutedand unsubstituted C₂-C₃₀ heteroaryl groups. In one embodiment, Z₁ and Z₂are each independently selected from C₆-C₁₂ aryl groups, and C₆-C₁₂haloaryl groups.

In Formula 3, nonlimiting examples of suitable substituents for Ar₁ andAr₂ include those represented by Formula 4 below.

In Formula 4, m may be an integer ranging from 1 to 5, and R₁, R₂ and R₃may be each independently selected from substituted and unsubstitutedC₁-C₁₀ alkyl groups, substituted and unsubstituted C₁-C₁₀ alkoxy groups,substituted and unsubstituted C₆-C₁₂ aryl groups, substituted andunsubstituted C₆-C₁₂ aryloxy groups, and substituted and unsubstitutedC₃-C₁₂ heteroaryl groups. Nonlimiting examples of suitable substituentsfor R₁, R₂ and R₃ include C₁-C₁₀ alkyl groups, phenyl groups, halophenylgroups, cyanophenyl groups, C₁-C₁₀ alkylphenyl groups, C₁-C₁₀alkoxyphenyl groups, biphenyl groups, halobiphenyl groups, naphthylgroups, halonaphthyl groups, C₁-C₁₀ alkylnaphthyl groups, and C₁-C₁₀alkoxynaphthyl groups.

Nonlimiting examples of suitable silanylamine-based compounds satisfyingFormula 1 include Compounds 1 to 168 below.

The silanylamine-based compound represented by Formula 1 may be preparedby various methods. According to one embodiment of the presentinvention, as shown in Reaction Scheme 1 below, a compound representedby Formula 1a is reacted with a compound represented by Formula 1b toprepare a silanylamine-based compound represented by Formula 1.

In Formulae 1a, 1b and 1, X, n, Ar₁, Ar₂, R₁, R₂ and R₃ are as describedabove, and Y is a halogen atom such as F, Cl, Br or I.

The reaction represented by Reaction Scheme 1 may be performed in thepresence of Pd₂(dba)₃ (where dba is dibenzylideneacetone), sodiumtert-butoxide and tri(tert-butyl)phosphine and may be performed at atemperature ranging from about 50 to about 150° C.

According to another embodiment of the present invention, an organiclight emitting device includes a first electrode, a second electrode andan organic layer positioned between the first electrode and the secondelectrode. The organic layer includes a silanylamine-based compoundrepresented by Formula 1. The organic layer including thesilanylamine-based compound represented by Formula 1 may be a holeinjection layer, a hole transport layer, or a single layer having bothhole injection and hole transport capabilities. The organic layerincluding the silanylamine-based compound represented by Formula 1 mayalso be an emissive layer. The emissive layer may include phosphorescentmaterials or fluorescent materials. The first electrode may be an anodeand the second electrode may be a cathode, or the first electrode may bea cathode and the second electrode may be an anode.

The organic light emitting device may further include at least one layerselected from a hole injection layer, a hole transport layer, anelectron blocking layer, an emissive layer, a hole blocking layer, anelectron transport layer and an electron injection layer. For example,the organic light emitting device may have a first electrode/holeinjection layer/emissive layer/second electrode structure, a firstelectrode/hole injection layer/hole transport layer/emissivelayer/electron transport layer/second electrode structure, or a firstelectrode/hole injection layer/hole transport layer/emissivelayer/electron transport layer/electron injection layer/second electrodestructure. The organic light emitting device may also have a firstelectrode/single layer/emissive layer/electron transport layer/secondelectrode structure, or a first electrode/single layer/emissivelayer/electron transport layer/electron injection layer/second electrodestructure, where the single layer has both hole injection and holetransport capabilities.

Hereinafter, a method of preparing an organic light emitting deviceaccording to one embodiment of the present invention will be describedwith reference to FIG. 1. FIG. 1 is a schematic showing an organic lightemitting device according to one embodiment of the present invention.The organic light emitting device illustrated in FIG. 1 includes asubstrate, a first electrode (anode), a hole injection layer, a holetransport layer, an emissive layer, an electron transport layer, anelectron injection layer and a second electrode (cathode).

According to one embodiment of the present invention, the firstelectrode is first formed by depositing or sputtering a highwork-function material on a substrate. The first electrode may be ananode or a cathode. The substrate can be any substrate used inconventional organic light emitting devices, and may be a glasssubstrate or a transparent plastic substrate that is waterproof and hasexcellent mechanical strength, thermal stability, transparency, surfacesmoothness and ease of handling. Nonlimiting examples of suitablematerials for forming the first electrode include ITO, IZO, SnO₂, ZnO,Al, Ag, Mg, and any material with high conductivity.

Then, the hole injection layer (HIL) may be formed on the firstelectrode by vacuum deposition, spin coating, casting, Langmuir Blodgett(LB) deposition, or the like.

When the HIL is formed using vacuum deposition, the depositionconditions may vary depending on the compound used to form the HIL, andthe structure and thermal properties of the HIL to be formed. Ingeneral, however, the vacuum deposition conditions may include adeposition temperature ranging from about 100 to about 500° C., apressure ranging from about 10⁻⁸ to about 10⁻³ torr, a depositionvelocity ranging from about 0.01 to about 100 Å/sec, and a layerthickness ranging from about 10 Å to 5 μm.

When the HIL is formed by spin coating, the coating conditions may varydepending on the compound used to form the HIL, and the structure andthermal properties of the HIL to be formed. In general, however, thecoating velocity may range from about 2000 to about 5000 rpm, and theheat treatment temperature (performed to remove solvent after coating)may range from about 80 to about 200° C.

The material used to form the HIL may be a silanylamine-based compoundrepresented by Formula 1 or may be a material known in the art.Nonlimiting examples of suitable materials for the HIL includephthalocyanine compounds (such as a copper phthalocyanine), star-bursttype amine derivatives (such as TCTA, m-MTDATA, and m-MTDAPB),polyaniline/Dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS) and similar solubleand conductive polymers.

The thickness of the HIL may range from about 100 to about 10000 Å. Inone embodiment, for example, the thickness of the HIL ranges from about100 to about 100 Å. When the thickness of the HIL is within theseranges, excellent hole injecting capabilities and driving voltages ofthe organic light emitting device may be obtained.

Then, the hole transport layer (HTL) may be formed on the HIL by vacuumdeposition, spin coating, casting, LB deposition, or the like. When theHTL is formed by vacuum deposition or spin coating, deposition andcoating conditions are similar to those for formation of the HIL,although the deposition and coating conditions may vary depending on thecompound used to form the HTL.

The material used to form the HTL may be a silanylamine-based compoundrepresented by Formula 1, or a material known in the art. Nonlimitingexamples of suitable materials for forming the HTL include carbazolederivatives (such as N-phenylcarbazole, polyvinylcarbazole and thelike), conventional amine derivatives having aromatic condensation rings(such as 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), and N,N′-di(naphthalene-1-yl)-N,N′-diphenyl benzydine (α-NPD)),and the like.

The thickness of the HTL may range from about 50 to about 1000 Å. In oneembodiment, for example, the thickness of the HTL ranges from about 100to about 600 Å. When the thickness of the HTL is within these ranges,excellent hole transporting capabilities and driving voltages of theorganic light emitting device may be obtained.

Then, the emissive layer (EML) may be formed on the HTL by vacuumdeposition, spin coating, casting, LB, or the like. When the EML isformed by vacuum deposition or spin coating, deposition and coatingconditions are similar to those for formation of the HIL, although thedeposition and coating conditions may vary depending on the compoundused to form the EML.

The material used to form the EML may be a silanylamine-based compoundrepresented by Formula 1 or various light emitting materials, such ashosts and dopants that are known in the art. The dopants may befluorescent and/or phosphorescent dopants that are known in the art.

Nonlimiting examples of suitable host materials include Alq₃,4,4′-N,N′-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK),distyrylarylene (DSA), or IDE215 from Idemitsu Co.

Nonlimiting examples of suitable fluorescent dopants include IDE102,IDE105 and IDE118 from Idemitsu Co. Nonlimiting examples of suitablephosphorescent dopants include Ir(ppy)₃ (green, where ppy is2-phenylpyridine) (green), (4,6-F2 ppy)₂Irpic, TEB002 from Covion Co.,platinum(II) octaethylporphyrin (PtOEP), compounds represented byFormula 5 below, Firpic, and red phosphorescent dopant RD 61 from UDCCo.

The amount of the dopant may range from about 0.1 to 20 parts by weightbased on 100 parts by weight of the material used to form the EML (i.e.,based on 100 parts by weight of the host and the dopant). In oneembodiment, for example, the amount of the dopant ranges from about 0.5to about 12 parts by weight based on 100 parts by weight of the materialused to form the EML. When the amount of the dopant is greater thanabout 0.1 parts by weight, the effect achieved by adding the dopant issufficient. Also, when the amount of the dopant is less than about 20parts by weight, fluorescence or phosphorescence quenching may beprevented.

The thickness of the EML may range from about 100 to about 1000 Å. Inone embodiment, for example, the thickness of the EML ranges from about200 to about 600 Å. When the thickness of the EML is within theseranges, excellent emitting abilities of the EML, and driving voltages ofthe organic light emitting device may be obtained.

When the EML includes a phosphorescent dopant, a hole blocking layer(HBL) (not shown) may be formed on the EML to prevent diffusion oftriplet excitons or holes into the electron transport layer. Nonlimitingexamples of suitable materials for forming the HBL include oxadiazolederivatives, triazole derivatives, phenanthroline derivatives, Balq, andBCP.

The thickness of the HBL may range from about 50 to about 1000 Å. In oneembodiment, for example, the thickness of the HBL ranges from about 100to about 300 Å. When the thickness of the HBL is within these ranges,excellent hole blocking abilities of the HBL and driving voltages of theorganic light emitting device may be obtained.

Then, the electron transport layer (ETL) may be formed on the HBL byvacuum deposition, spin coating, casting, or the like. When the ETL isformed by vacuum deposition or spin coating, deposition and coatingconditions are similar to those for formation of the HIL, although thedeposition and coating conditions may vary depending on the compoundused to form the ETL.

Nonlimiting examples of suitable materials for forming the ETL includequinoline derivatives (for example, tris(8-quinolinorate)aluminum(Alq₃)), TAZ, and the like.

The thickness of the ETL may range from about 100 to about 1000 Å. Inone embodiment, for example, the thickness of the ETL ranges from about100 to about 500 Å. When the thickness of the ETL is within theseranges, excellent electron transporting abilities of the ETL and drivingvoltages of the organic light emitting device may be obtained.

Then, the electron injection layer (EIL) may be formed on the ETL forexample, by vacuum deposition, spin coating, casting, or the like. TheEIL is formed of a material that allows easy injection of electrons froma cathode.

Nonlimiting examples of suitable materials for forming the EIL includeLiF, NaCl, CsF, Li₂O, BaO, and the like. Deposition and coatingconditions are similar to those for formation of the HIL, although thedeposition and coating conditions may vary depending on the materialused to form the EIL.

The thickness of the EIL may range from about 1 to about 100 Å. In oneembodiment, for example, the thickness of the EIL ranges from about 5 toabout 90 Å. When the thickness of the EIL is within these ranges,excellent electron injection abilities of the EIL and driving voltagesof the organic light emitting device may be obtained.

Finally, the second electrode can be formed on the EIL by vacuumdeposition, sputtering, or the like. The second electrode can be used asa cathode or an anode. The material used to form the second electrodemay be a low work-function metal, alloy, electrically conductivecompound, or a combination thereof. Nonlimiting examples of suitablematerials for the second electrode include Li, Mg, Al, Al—Li, Ca, Mg—In,Mg—Ag, and the like. In addition, a transparent cathode formed of ITO orIZO can be used to produce a front surface light emitting device.

Hereinafter, Synthesis Examples of Compounds 9, 43, 44, 45, and 137 andExamples are presented. However, the Synthesis Examples and Examples arepresented for illustrative purposes only and are not intended to limitthe scope of the present invention.

SYNTHESIS EXAMPLE 1

Synthesis of Compound 9

Compound 9 was synthesized via Reaction Scheme 2 below:

Synthesis of Intermediate A

3.12 g (10 mmol) of dibromobiphenyl was dissolved in 30 mL of THF, and 4mL of 2.5M n-butyllithium (in Hexane) was added thereto at −78° C. 2.95g (10 mmol) of chlorotriphenylsilane dissolved in 5 mL of THF wasgradually added thereto at −78° C. after one hour. The mixture wasstirred at room temperature for 5 hours, water was added thereto and themixture was washed three times with 30 mL of diethylether. The washeddiethylether layer was dried over MgSO₄ and dried under reduced pressureto obtain a product. The obtained product was purified by silica gelcolumn chromatography to obtain 2.9 g of white solid intermediate A(Yield: 60%). (¹H NMR (CDCl₃, 400 MHz) δ (ppm) 7.65-7.53 (m, 12H),7.47-7.36 (m, 11H)).

Synthesis of Compound 9

4.9 g (10 mmol) of intermediate A, 2.6 g (12 mmol) of2-naphthylphenylamine, 2.9 mg (30 mmol) of t-BuONa, 183 mg (0.2 mmol) ofPd₂(dba)₃, 40 mg (0.2 mmol) of P(t-Bu)₃ were dissolved in 40 mL oftoluene and stirred at 90° C. for three hours.

When the reaction was completed, the mixture was cooled to roomtemperature and extracted three times with 40 mL of distilled water anddiethylether. A collected organic layer was dried over MgSO₄ toevaporate the solvent. The residue was purified using silica gel columnchromatography to obtain 5.67 g of yellow solid Compound 9 (Yield: 90%).(¹H NMR (CD₂Cl₂, 400 MHz) δ (ppm) 7.75 (t, 2H), 7.63-7.56 (m, 12H), 7.53(d, 2H), 7.46-7.34 (m, 12H), 7.30-7.26 (m, 3H), 7.16 (d, 4H), 7.06 (t,1H); ¹³C NMR (CD₂Cl₂, 100 MHz) δ (ppm) 147.6, 147.5, 145.3, 141.7,136.9, 136.3, 134.8, 134.5, 134.2, 132.4, 130.2, 129.7, 129.4, 128.9,127.9, 127.8, 127.5, 126.9, 126.3, 126.0, 124.8, 124.6, 124.5, 124.0,123.3, 120.5).

The UV absorption spectrum of 0.2 mM of the obtained Compound 9 dilutedin CH₂Cl₂ was measured, and the maximum absorption spectrum was 340 nm.

Deposition temperature (Td) and glass transition temperature (Tg) weremeasured by performing thermal analysis using thermo gravimetricanalysis (TGA) and differential scanning calorimetry (DSC) under thefollowing conditions: N₂ atmosphere, temperatures of room temperature to600° C. (10° C./min) for TGA and room temperature to 400° C. for DSC,and Pan Type: Pt Pan in disposable Al Pan (TGA) and disposable Al pan(DSC). Td was 330° C., and Tg was 97° C.

The highest occupied molecular orbital (HOMO) and lowest occupiedmolecular orbital (LUMO) were measured using the UV absorption spectrumand an ionization potential measurement AC-2. The HOMO was 5.4 eV andthe LUMO was 2.33 eV.

SYNTHESIS EXAMPLE 2

Synthesis of Compound 43

Compound 43 was synthesized via Reaction Scheme 3 below:

Synthesis of Intermediate B

3.69 g (10.0 mmol) of 3-iodo-9-phenylcarbazole, 1.11 g (12.0 mmol) ofaniline, 2.88 g (30.0 mmol) of t-BuONa, 183 mg (0.2 mmol) of Pd₂(dba)₃,40 mg (0.2 mmol) of P(t-Bu)₃ were dissolved in 40 mL of toluene, andstirred at 90° C. for 3 hours.

When the reaction was completed, the mixture was cooled to roomtemperature and distilled water was added thereto. The mixture wasextracted three times with 40 mL of diethylether. A collected organiclayer was dried over MgSO₄ to evaporate the solvent. The residue waspurified using silica gel column chromatography to obtain 2.17 g ofwhite solid Intermediate B (Yield: 65%). (¹H NMR (CDCl₃, 400 MHz) δ(ppm) 8.01 (m, 1H), 7.66 (m, 1H), 7.51-7.33 (m, 7H), 7.21-6.94 (m, 5H),6.73 (m, 1H), 5.68 (bs, 1H); ¹³C NMR (CDCl₃, 100 MHz) δ (ppm) 144.6,139.8, 137.4, 135.7, 129.8, 129.3, 128.0, 127.4, 127.1, 126.5, 119.1,119.0, 118.6, 118.4, 116.7, 113.1, 111.1, 109.4, 102.4).

Synthesis of Compound 43

Compound 43 was obtained as in Synthesis Example 1, except thatIntermediate B was used instead of 2-naphthylphenylamine (Yield: 82%).(¹H NMR (CDCl₃, 300 MHz) δ (ppm) 7.98 (d, 1H), 7.69 (bd, 1H), 7.67-7.54(m, 14H), 7.50-7.33 (m, 14H), 7.28-7.13 (m, 9H), 6.97 (t, 1H); DEPT ¹³CNMR (CDCl₃, 100 MHz) δ (ppm) 136.9, 136.5, 130.0, 129.6, 129.2, 127.9,127.7, 127.5, 127.1, 126.2, 126.0, 125.8, 123.3, 122.3, 122.1, 120.6,120.0, 118.8, 110.8, 110.0).

The UV absorption spectrum of 0.2 mM of the obtained Compound 43 dilutedin CH₂Cl₂ was measured, and the maximum absorption spectrum was 345 and310 nm.

Td and Tg were measured by performing thermal analysis using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC)under the following conditions: N₂ atmosphere, temperatures of roomtemperature to 600° C. (10° C./min) for TGA and of room temperature to400° C. for DSC, and Pan Type: Pt Pan in disposable Al Pan (TGA) anddisposable Al pan (DSC). Td was 380° C., and Tg was 127° C.

The HOMO and LUMO were measured using the UV absorption spectrum and anionization potential measurement AC-2. The HOMO was 5.30 eV and the LUMOwas 2.24 eV.

SYNTHESIS EXAMPLE 3

Synthesis of Compound 44

Compound 44 was synthesized via Reaction Scheme 4 below:

Synthesis of Intermediate C

Intermediate C was synthesized as in Synthesis Example 1, except thatbenzylamine was used instead of aniline. (NMR (CDCl₃, 400 MHz) δ (ppm)8.02 (m, 1H), 7.67 (m, 1H), 7.52-7.31 (m, 7H), 7.02-6.86 (m, 5H), 6.10(bs, 1H), 2.25 (s, 3H); ¹³C NMR (CDCl₃, 100 MHz) δ (ppm) 140.1, 138.8,136.4, 134.7, 128.8, 127.3, 127.0, 126.4, 126.1, 125.5, 118.1, 118.0,117.6, 117.4, 116.7, 112.1, 110.1, 108.4, 101.4, 20.3).

Synthesis of Compound 44

Compound 44 was obtained as in Synthesis Example 1, except thatIntermediate C was used instead of 2-naphthylphenylamine (Yield: 87%).(¹H NMR (CDCl₃, 400 MHz) δ (ppm) 8.09 (d, 1H), 8.01 (d, 1H), 7.70-7.52(m, 17H), 7.49-7.35 (m, 12H), 7.24-7.18 (m, 2H), 7.11 (d, 2H), 7.04 (t,4H), 2.28 (t, 3H); ¹³C NMR (CDCl₃, 100 MHz) δ (ppm) 149.5, 146.4, 142.6,142.2, 141.3, 138.9, 138.3, 137.5, 137.0, 135.0, 133.2, 133.1, 132.6,130.9, 130.7, 130.5, 128.8, 128.5, 128.3, 127.7, 127.1, 126.5, 125.2,125.0, 123.8, 121.9, 121.4, 120.8, 119.3, 111.5, 110.6, 20.7).

The UV absorption spectrum of 0.2 mM of the obtained Compound 44 dilutedin CH₂Cl₂ was measured, and the maximum absorption spectrum was 343,313, and 245 nm.

Td and Tg were measured by performing thermal analysis using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC)under the following conditions: N₂ atmosphere, temperatures of roomtemperature to 600° C. (10° C./min) for TGA and of room temperature to400° C. for DSC, and Pan Type: Pt Pan in disposable Al Pan (TGA) anddisposable Al pan(DSC). Td was 414° C., and Tg was 129° C.

The HOMO and LUMO were measured using the UV absorption spectrum and anionization potential measurement AC-2. The HOMO was 5.20 eV and the LUMOwas 2.21 eV.

SYNTHESIS EXAMPLE 4

Synthesis of Compound 45

Compound 45 was synthesized via Reaction Scheme 5 below:

Synthesis of Intermediate D

Intermediate D was synthesized as in Synthesis Example 1, except thatfluoroaniline was used instead of aniline. (NMR (CDCl₃, 400 MHz) δ (ppm)8.02 (m, 1H), 7.97-7.92 (m, 2H), 7.66 (m, 1H), 7.48-7.18 (m, 9H), 6.94(m, 1H), 6.50 (bs, 1H); ¹³C NMR (CDCl₃, 100 MHz) δ (ppm) 157.8 (d),140.7 (d), 137.8, 135.4, 133.7, 127.8, 126.3, 126.0, 125.4, 125.1,124.5, 117.1, 117.0, 116.6, 116.4, 115.7, 111.1, 109.1, 107.4, 100.4).

Synthesis of Compound 45

Compound 45 was obtained as in Synthesis Example 1, except thatIntermediate D was used instead of 2-naphthylphenylamine (Yield: 80%).(¹H NMR (Acetone-d6, 400 MHz) δ (ppm) 8.06 (d, 1H), 8.02 (d, 1H),7.68-7.50 (m, 16H), 7.47-7.34 (m, 13H), 7.21-7.13 (m, 4H), 7.07-7.00 (m,4H); ¹³C NMR (CDCl₃, 100 MHz) δ (ppm) 159.8, 157.4, 148.7, 144.5, 141.8,141.4, 140.3, 138.2, 137.5, 136.8, 136.2, 134.2, 132.8, 131.9, 130.1,129.8, 128.0, 127.7, 127.6, 126.9, 126.4, 125.9, 125.8, 125.6, 124.5,123.0, 121.2, 120.6, 120.1, 118.5, 116.1, 115.8, 110.9, 109.8).

The UV absorption spectrum of 0.2 mM of the obtained Compound 45 dilutedin CH₂Cl₂ was measured, and the maximum absorption spectrum was 338,309,and 243 nm.

Td and Tg were measured by performing thermal analysis using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC)under the following conditions: N₂ atmosphere, temperatures of roomtemperature to 600° C. (10° C./min) for TGA and of room temperature to400° C. for DSC, and Pan Type: Pt Pan in disposable Al Pan (TGA) anddisposable Al pan(DSC). Td was 405° C., and Tg was 126° C.

The HOMO and LUMO were measured using the UV absorption spectrum and anionization potential measurement AC-2. The HOMO was 5.20 eV and the LUMOwas 2.22 eV.

SYNTHESIS EXAMPLE 5

Synthesis of Compound 137

Compound 137 was synthesized via Reaction Scheme 6 below:

Synthesis of Intermediate E

3.25 g (10.0 mmol) of 3, 6-dibromocarbazole, 10.2 g (50.0 mmole)iodobenzene, 190 mg (1.0 mmole) of CuI, 132 mg (0.5 mmole) of 18-C-6,2.76 g (20.0 mmole) of K₂CO₃ were dissolved in 50 mL of DMPU, andstirred at 170° C. for 20 hours. The mixture was cooled to roomtemperature and 50 mL of diethylether was added thereto. Then themixture was washed with plenty of water and ammonium hydroxide solution.A collected organic layer was dried over MgSO₄ to evaporate the solvent.The residue was purified using silica gel column chromatography toobtain 3.40 g of white solid Intermediate E (Yield: 85%). (NMR (CDCl₃,400 MHz) δ (ppm) 7.92 (m, 2H), 7.55-7.47 (m, 6H), 7.36-7.16 (m, 3H); ¹³CNMR (CDCl₃, 100 MHz) δ (ppm) 142.6, 137.6, 130.2, 129.8, 127.4, 127.0,122.8, 122.5, 115.3, 111.3).

Synthesis of Intermediate F

4.01 g (10 mmol) of Intermediate E was dissolved in 20 mL of THF, and4.6 mL (12.0 mmol) of 2.6M n-butyllithium (in Hexane) was added theretoat −78° C. for 10 minutes. 3.83 g (13.0 mmol) of chlorotriphenylsilanedissolved in 20 mL of THF was gradually added thereto at −78° C. for 20minutes, and the mixture was stirred at room temperature for 17 hours.50 mL of water was added to the mixture and the mixture was extractedtwice with 50 mL of diethylether. A collected organic layer was driedover MgSO₄ to evaporate the solvent. The residue was purified usingsilica gel column chromatography to obtain 3.19 g of white solidIntermediate F (Yield: 55%). (NMR (CDCl₃, 400 MHz) δ (ppm) 8.28-8.21 (m,3H), 8.14 (d, 2H), 7.86-7.14 (m, 21H); ¹³C NMR (CDCl₃, 100 MHz) δ (ppm)143.1, 137.9, 136.4, 134.4, 133.9, 133.7, 129.8, 129.5, 129.0, 128.0,127.9, 127.5, 126.9, 124.9, 123.9, 123.1, 118.3, 111.2, 109.7, 107.6).

Synthesis of Compound 137

Compound 137 was obtained as in Synthesis Example 2, except thatIntermediate F was used instead of Intermediate A (Yield: 80%). (¹H NMR(CDCl₃, 300 MHz) δ (ppm) 8.25 (s, 1H), 7.94 (d, 3H), 7.64-7.52 (m, 15H),7.43-7.24 (m, 18H), 7.20-7.14 (m, 3H), 7.02 (d, 2H), 6.83 (t, 1H)).

The UV absorption spectrum of 0.2 mM of the obtained Compound 137diluted in CH₂Cl₂ was measured, and the maximum absorption spectrum was317 nm.

Td and Tg were measured by performing thermal analysis using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC)under the following conditions: N₂ atmosphere, temperatures of roomtemperature to 600° C. (10° C./min) for TGA and of room temperature to400° C. for DSC, and Pan Type: Pt Pan in disposable Al Pan (TGA) anddisposable Al pan (DSC). Td was 390° C., and Tg was 148° C.

The HOMO and LUMO were measured using the UV absorption spectrum and anionization potential measurement AC-2. The HOMO was 5.1 eV and the LUMOwas 2.15 eV.

EXAMPLE 1

A Corning 15Ω/cm² (1,200 Å) ITO glass substrate was cut into 50 mm×50mm×0.7 mm size pieces, ultrasonicwashed with isopropyl alcohol for 5minutes, ultrasonicwashed with deionized water for 5 minutes, and washedwith UV ozone for 30 minutes. Then, the glass substrate was installed ina vacuum deposition device.

Compound 9 was vacuum deposited on the substrate to form a HIL with athickness of 600 Å. 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB)was vacuum deposited on the HIL to form a HTL with a thickness of 300 Å.

IDE215 (a blue fluorescent host obtained from Idemitsu Co.) and IDE118(a blue fluorescent dopant obtained from Idemitsu Co.) (98:2, w/w) werevacuum deposited on the HTL to form an EML with a thickness of 300 Å.

Then, Alq₃ was vacuum deposited on the EML to form an ETL with athickness of 300 Å, LiF was vacuum deposited on the ETL to form an EILwith a thickness of 10 Å, and Al was vacuum deposited on the EIL to athickness of 3000 Å (cathode) to form a LiF/Al electrode to complete themanufacture of an organic light emitting device.

EXAMPLE 2

An organic light emitting device was prepared as in Example 1, exceptthat Compound 43 was used instead of Compound 9 in forming the HIL.

EXAMPLE 3

An organic light emitting device was prepared as in Example 1, exceptthat Compound 44 was used instead of Compound 9 in forming the HIL.

EXAMPLE 4

An organic light emitting device was prepared as in Example 1, exceptthat Compound 45 was used instead of Compound 9 in forming the HIL.

EXAMPLE 5

An organic light emitting device was prepared as in Example 1, exceptthat Compound 137 was used instead of Compound 9 in forming the HIL.

COMPARATIVE EXAMPLE 1

An organic light emitting device was prepared as in Example 1, exceptthat IDE406 (from Idemitsu Co.) was used instead of Compound 9 informing the HIL.

EVALUATION EXAMPLE

The driving voltage, current density, luminance, current efficiency andcolor coordinates of the organic light emitting devices obtainedaccording to Examples 1 to 5 and Comparative Example 1 were measuredusing a Spectroscan spectrometer (PR650 from Photo Research Inc.). Theresults are shown in Table 1 below. FIG. 2 is a graph of luminanceaccording to driving voltage of the organic light emitting devicesaccording to Example 1 and Comparative Example 1, FIG. 3 is a graph ofluminance according to driving voltage of the organic light emittingdevices according to Example 2 and Comparative Example 1, and FIG. 4 isa graph of luminance according to time (100 mA/cm²) of the organic lightemitting devices according to Example 3 and Comparative Example 1.

TABLE 1 Driving Current Current Color voltage density Luminanceefficiency coordinate (V) (mA/cm²) (cd/m²) (cd/A) (x, y) Example 1 6.7410 1,036 10.36 0.146, 0.268 8.04 100 12,030 12.03 0.146, 0.260 Example 25.90 10 916 9.16 0.139, 0.244 7.68 100 9,352 9.35 0.139, 0.239 Example 35.78 10 663 6.63 0.144, 0.239 7.34 100 6,882 6.88 0.144, 0.233 Example 46.34 10 581 5.81 0.144, 0.229 8.18 100 6,459 6.46 0.144, 0.223 Example 55.52 10 610 6.10 0.144, 0.235 7.78 100 6,360 6.36 0.144, 0.233 Com- 6.3510 635 6.35 0.144, 0.229 parative 8.07 100 6,309 6.31 0.144, 0.223Example 1

As shown in Table 1, the organic light emitting devices preparedaccording to Examples 1 to 5 had better I-V-L characteristics comparedto the organic light emitting device prepared according to ComparativeExample 1. In particular, the organic light emitting device of Example 1having an organic layer including Compound 9 as the HIL, and the organiclight emitting device of Example 2 having an organic layer includingCompound 43 as the HIL showed improved brightness compared to theorganic light emitting device of Comparative Example 1 (Refer to FIGS. 2and 3). In addition, the organic light emitting devices of Examples 1 to5 had similar color coordinate characteristics to that of ComparativeExample 1. The organic light emitting device of Example 3 had a longerlifetime than that of Comparative Example 1.

The silanylamine-based compounds according to the present invention haveexcellent electrical stability and high electron transportingcapabilities. Thus, the silanylamine-based compounds of the presentinvention may be effectively used for red, green, blue, and whitefluorescent and phosphorescent materials used to form HILs, HTLs, andEMLs in organic light emitting devices. Organic light emitting deviceshaving high efficiency, low driving voltage, high brightness and longlifetime may be prepared using the silanylamine-based compounds of thepresent invention.

While the present invention has been illustrated and described withreference to certain exemplary embodiments, it is understood by those ofordinary skill in the art that various changes and modifications can bemade to the described embodiments without departing from the spirit andscope of the present invention as defined by the following claims.

1. A compound comprising a silanylamine-based compound represented byFormula 1:

wherein: X is selected from the group consisting of a single bond,substituted C₁-C₃₀ alkylene groups, unsubstituted C₁-C₃₀ alkylenegroups, substituted C₆-C₃₀ arylene groups, unsubstituted C₆-C₃₀ arylenegroups, substituted C₂-C₃₀ heteroarylene groups and unsubstituted C₂-C₃₀heteroarylene groups; n is an integer ranging from 1 to 5; Ar₁ isselected from the group consisting of substituted C₂-C₃₀ heteroarylgroups, and unsubstituted C₂-C₃₀ heteroaryl groups; Ar₂ is selected fromthe group consisting of substituted C₆-C₃₀ aryl groups, andunsubstituted C₆-C₃₀ aryl groups; R₁, R₂ and R₃ are each independentlyselected from the group consisting of hydrogen atoms, substituted C₁-C₃₀alkyl groups, unsubstituted C₁-C₃₀ alkyl groups, substituted C₂-C₃₀alkenyl groups, unsubstituted C₂-C₃₀ alkenyl groups, substituted C₂-C₃₀alkynyl groups, unsubstituted C₂-C₃₀ alkynyl groups, substituted C₁-C₃₀alkoxy groups, unsubstituted C₁-C₃₀ alkoxy groups, substituted C₆-C₃₀aryloxy groups, unsubstituted C₆-C₃₀ aryloxy groups, substituted C₆-C₃₀aryl groups, unsubstituted C₆-C₃₀ aryl groups, substituted C₂-C₃₀heteroaryl groups and unsubstituted C₂-C₃₀ heteroaryl groups; and atleast two of R₁, R₂ and R₃ are optionally bonded to each other to form asaturated or unsaturated ring.
 2. The compound of claim 1, wherein X isselected from the group consisting of substituted C₁-C₁₀ alkylenegroups, unsubstituted C₁-C₁₀ alkylene groups, substituted phenylenegroups, unsubstituted phenylene groups, substituted naphthylene groups,unsubstituted naphthylene groups, substituted fluorenylene groups,unsubstituted fluorenylene groups, substituted anthracenylene groups,unsubstituted anthracenylene groups, substituted pyridinylene groups,unsubstituted pyridinylene groups, substituted quinolylene groups,unsubstituted quinolylene groups, substituted isoquinolylene groups,unsubstituted isoquinolylene groups, substituted anthraquinolylenegroups, unsubstituted anthraquinolylene groups, substitutedcarbazolylene groups, and unsubstituted carbazolylene groups.
 3. Thecompound of claim 1, wherein X is selected from the group consisting ofsubstituents listed in Formula 2:

wherein R₄ and R₅ are each independently selected from the groupconsisting of hydrogen atoms, halogen atoms, cyano groups, hydroxylgroups, substituted C₁-C₃₀ alkyl groups, unsubstituted C₁-C₃₀ alkylgroups, substituted C₁-C₃₀ alkoxy groups, unsubstituted C₁-C₃₀ alkoxygroups, substituted C₆-C₃₀ aryl groups, unsubstituted C₆-C₃₀ arylgroups, substituted C₃-C₃₀ heteroaryl groups, and unsubstituted C₃-C₃₀heteroaryl groups.
 4. The compound of claim 3, wherein R₄ and R₅ areeach independently selected from the group consisting of phenyl groupsand halophenyl groups.
 5. The compound of claim 1, wherein —(X)_(n)— isselected from the group consisting of substituents listed in Formula 3:


6. The compound of claim 1, wherein Ar₁ is selected from the groupconsisting of substituted C₃-C₁₅ heteroaryl groups and unsubstitutedC₃-C₁₅ heteroaryl groups, and Ar₂ is selected from the group consistingof substituted C₆-C₁₂ aryl groups, and unsubstituted C₆-C₁₂ aryl groups.7. The compound of claim 1, wherein Ar₁ is selected from the groupconsisting of-carbazolyl groups, halocarbazolyl groups, cyanocarbazolylgroups, C₁-C₅ alkylcarbazolyl groups, C₁-C₅ alkoxycarbazolyl groups,phenoxycarbazolyl groups, carbazolyl groups substituted with —N(Z₁)(Z₂),C₆-C₁₂ arylcarbazolyl groups, C₆-C₁₂ haloarylcarbazolyl groups, pyridylgroups, halopyridyl groups, cyanopyridyl groups, C₁-C₅ alkylpyridylgroups, C₁-C₅ alkoxypyridyl groups, phenoxypyridyl groups, and pyridylgroups substituted with —N(Z₁)(Z₂); Ar₂ is selected from the groupconsisting of phenyl groups, halophenyl groups, cyanophenyl groups,C₁-C₅ alkylphenyl groups, C₁-C₅ alkoxyphenyl groups, phenoxyphenylgroups, phenyl groups substituted with —N(Z₁)(Z₂), biphenyl groups,halobiphenyl groups, cyanobiphenyl groups, C₁-C₅ alkylnaphthyl groups,C₁-C₅ alkoxynaphthyl groups, phenoxynaphthyl groups, naphthyl groupssubstituted with —N(Z₁)(Z₂), fluorenyl groups, halofluorenyl groups,cyanofluorenyl groups, C₁-C₅ alkylfluorenyl groups, C₁-C₅alkoxyfluorenyl groups, and phenoxyfluorenyl groups; wherein Z₁ and Z₂are each independently selected from the group consisting of hydrogenatoms, substituted C₁-C₃₀ alkyl groups, unsubstituted C₁-C₃₀ alkylgroups, substituted C₁-C₃₀ haloalkyl groups, unsubstituted C₁-C₃₀haloalkyl groups, substituted C₆-C₃₀ aryl groups, unsubstituted C₆-C₃₀aryl groups, substituted C₆-C₃₀ haloaryl groups, unsubstituted C₆-C₃₀haloaryl groups, substituted C₂-C₃₀ heteroaryl groups and unsubstitutedC₂-C₃₀ heteroaryl groups.
 8. The compound of claim 7, wherein Z₁ and Z₂are each independently selected from the group consisting of C₆-C₁₂ arylgroups and C₆-C₁₂ haloaryl groups.
 9. The compound of claim 1, whereinAr₁ is selected from the group consisting of substituents listed inFormula 4A and Ar₂ is selected from the group consisting of substituentslisted in Formula 4B:

wherein m is an integer ranging from 1 to
 5. 10. The compound of claim1, wherein R₁, R₂, and R₃ are each independently selected from the groupconsisting of substituted C₁-C₁₀ alkyl groups, unsubstituted C₁-C₁₀alkyl groups, substituted C₁-C₁₀ alkoxy groups, unsubstituted C₁-C₁₀alkoxy groups, substituted C₆-C₁₂ aryl groups, unsubstituted C₆-C₁₂ arylgroups, substituted C₆-C₁₂ aryloxy groups, unsubstituted C₆-C₁₂ aryloxygroups, substituted C₃-C₁₂ heteroaryl groups and unsubstituted C₃-C₁₂heteroaryl groups.
 11. The compound of claim 1, wherein R₁, R₂ and R₃are each independently selected from the group consisting of C₁-C₁₀alkyl groups, phenyl groups, halophenyl groups, cyanophenyl groups,C₁-C₁₀ alkylphenyl groups, C₁-C₁₀ alkoxyphenyl groups, biphenyl groups,halobiphenyl groups, naphthyl groups, halonaphthyl groups, C₁-C₁₀alkylnaphthyl groups, and C₁-C₁₀ alkoxynaphthyl groups.
 12. The compoundof claim 1, wherein the silanylamine-based compound is selected from thegroup consisting of Compounds 43, 44, 45 and 137:


13. A method of preparing a silanylamine-based compound represented byFormula 1 comprising reacting a compound represented by Formula 1a and acompound represented by Formula 1b by Reaction Scheme 1:

wherein: X is selected from the group consisting of a single bond,substituted C₁-C₃₀ alkylene groups, unsubstituted C₁-C₃₀ alkylenegroups, substituted C₆-C₃₀ arylene groups, unsubstituted C₆-C₃₀ arylenegroups, substituted C₂-C₃₀ heteroarylene groups and unsubstituted C₂-C₃₀heteroarylene groups; n is an integer ranging from 1 to 5; Ar₁ isselected from the group consisting of substituted C₂-C₃₀ heteroarylgroups, and unsubstituted C₂-C₃₀ heteroaryl groups; Ar₂ is selected fromthe group consisting of substituted C₂-C₃₀ heteroaryl groups, andunsubstituted C₂-C₃₀ heteroaryl groups; R₁, R₂ and R₃ are eachindependently selected from the group consisting of hydrogen atoms,substituted C₁-C₃₀ alkyl groups, unsubstituted C₁-C₃₀ alkyl groups,substituted C₂-C₃₀ alkenyl groups, unsubstituted C₂-C₃₀ alkenyl groups,substituted C₂-C₃₀ alkynyl groups, unsubstituted C₂-C₃₀ alkynyl groups,substituted C₁-C₃₀ alkoxy groups, unsubstituted C₁-C₃₀ alkoxy groups,substituted C₆-C₃₀ aryloxy groups, unsubstituted C₆-C₃₀ aryloxy groups,substituted C₆-C₃₀ aryl groups, unsubstituted C₆-C₃₀ aryl groups,substituted C₂-C₃₀ heteroaryl groups and unsubstituted C₂-C₃₀ heteroarylgroups; at least two of R₁, R₂ and R₃ are optionally bonded to eachother to form a saturated or unsaturated ring; and Y is a halogen atom.14. An organic light emitting device comprising: a first electrode; asecond electrode; and an organic layer positioned between the firstelectrode and the second electrode, wherein the organic layer comprisesthe compound of claim
 1. 15. The organic light emitting device of claim14, wherein the organic layer comprises one or more layers selected fromthe group consisting of hole injection layers, emissive layers, holetransport layers and electron transport layers.
 16. The organic lightemitting device of claim 14, wherein the organic layer comprises asingle layer having both hole injection and hole transport capabilities.17. The organic light emitting device of claim 15 having a structureselected from the group consisting of first electrode/hole injectionlayer/emissive layer/second electrode structures, first electrode/holeinjection layer/hole transport layer/emissive layer/electron transportlayer/second electrode structures, and first electrode/hole injectionlayer/hole transport layer/emissive layer /electron transportlayer/electron injection layer/second electrode structures.
 18. Theorganic light emitting device of claim 17 further comprising a layerselected from the group consisting of hole blocking layers, electronblocking layers and combinations thereof.
 19. The organic light emittingdevice of claim 16, wherein the organic light emitting device comprisesa structure selected from the group consisting of: firstelectrode/single layer having both hole injection and hole transportcapabilities/emissive layer/electron transport layer/second electrodestructures, and first electrode/single layer having both hole injectionand hole transport capabilities/emissive layer/electron transportlayer/electron injection layer/second electrode structures.
 20. Theorganic light emitting device of claim 19 further comprising a layerselected from the group consisting of hole blocking layers, electronblocking layers and combinations thereof.
 21. The organic light emittingdevice of claim 14, wherein the organic layer comprises an emissivelayer.
 22. The organic light emitting device of claim 21, wherein theemissive layer comprises a material selected from the group consistingof phosphorescent materials and fluorescent materials.